Anthracene dyes and process of making same.



UNITED STATES P ENT, OFFICE.

MAX HENRY ISLER, OF MANNHEIM, GERMANY, ASSIGNOR TO IBADISCHE ANILIN &

SODA FABRIK, F LUDWIGSHAFEN-ON- THE-RHINE, GERMANY, ACORPORATION.

ANTHRAGENE IDYES AND PROCESS OF MAKING-SAME.

.No Drawing.

Specification of Letters Patent. Application filed January 31, 1911.Serial No. 605,746.

Patented May 14, 1912.

amino-anthraquinone, with trichlor-methylsulfur chlorid(perchlor-methyl-mercaptan, cf. 13074072750, 20, 2377) I can obtain newcompounds which are dianthraquinonylthiourea bodies which can either beused as.

coloring matters themselves for dyeing cotton or wool from a vat, or canbe employed in the production of coloring matters.- The reactionaccording to this invention isipreferably carried out in the presence ofa solvent or a suspension agent and, if desired, also in the presence ofa substance exercising a catalytic action, such for example as copper orcopper salts, and also, if desired, a body which is capable of fixinghydrochloric acid may be added. 1.

The following is an example of how my invention can be carried intopractical effeet, but the invention is not limited to this example.v Theparts are by weight. Boil together, in a reflux apparatus, ten parts of2-amino-anthraquinone, from fifty to one hundred parts ofnitrobenzene,;and four chlorid,

parts of trichlor-methyl-sulfur until, by a test, it is seen thatcoloring matter is no longer being formed; The condensation productshould then be filtered ofl", preferably While hot. It can be purifiedby re-crystallizing itfrom quinolin and then, from analysis, appears topossess a constitution corresponding to the formula Itdissolves inconcentrated sulfuric acid, the solution being orange, but it isdiiiicultly soluble in alcohol, benzene, nitroben zene, and glacialacetic acid. It yields a reddish orange colored vat in alkalinehydrosulfite and this colors cotton brown-red shades, which becomeorange color upon washing and hanging in the air. Wool can be'dyed in asimilar manner.

can be carried on, if desired, at'a considerably lower temperature, forinstance at about onehundred and thirty degrees centigrade, but, in thiscase, a longer time is re; quired for the completion of the reaction.

' Instead of Q-amino-anthraquinonc, a dcrivative thereof, or adiamino-antl-iraquinone, or a derivative thereof, can be employed andcorresponding results be obtained. For example, the coloring mattersobtained according to this invention from the followingamino-anthraquinones will produce the following colors on cotton andwool :2.6-diamino-anthraquinone, yellow -In the foregoing example, thereaction Q-amino-6-hydroxy-anthraquinone, brown the amino-anthraquinoneor derivative.

2-amino-3-methyl-anthraquinone, orange; Someof the roperties of othercoloring 2-amino-8 -chloranthraquinone, yellowmatters obtaina leaccording to my mvenolive. tion are given in the followmg table--Solution in- Dye from trichlor-methyl-sulfur A pearance Com-r of vatShade on chlor 0? powder Concentrated Boiling nltro- Bolling cottonsulfuric acid. benzene. 7V caustlcsoda. 1.4-diamino-anthraquinoneBlue-black. Brown Brown-vi0let.... Insolub1e.. Dull rednnl. Violet-gray.

Alpha-beta-dlamino-anthraquinone. Brown-violet Brown-olive.....Yellowishbrown Inso1ub1e Yellowish'red. Brown-red.

Para-dlamino-anthrhrufln Lustrous Brown Red-violet Blue Brown Blue-gray.

blue-violet.

2'-amino-anthraqulnone... Brick-rem... Orange Yelloiv Insoluhle Reddish01 Orange.

' ange.

l-amino-anthraquinone Dark gray... Olive Yellowishbrown Insoluble..Brown-red.... Brown.

1.4-aminc-hydroxy-anthraquinone B1ue-violet.. Blue Red ..-BlueRed-brown... Gray-violet.

LB-diamino-anthraquinone Brown Yellowlshbrown Yellowishbrown Insoluble"Yellowishred. Violet-brown.

In ,the case of lA-diamino-anthraquinone,

two molecular proportions thereof were allowed to' react on twomolecular proportions of trichlor-methyl-sulfur chlorid. In all theother cases, only one molecular proportion of the trichlor-methyl-sulfurchlorid was taken for two molecular proportions 0:;

course the invention isnot limited to the actual proportions here statedby way of example. The alpha beta diamino anthraquinone mentioned in theforegoing table thra uinone for the production of 1.5- and1.8-d1nitro-anthraquinone.

Now what I claim is 1.- The process of producin coloring matters of theanthracene series y treating an amino-anthraquinone body witht-richlormethyl-sulfur chlorid.

2; The process of producing coloring. matter of the anthracene series bytreatin 2- amino-ant-hraquinone with trichlor-met ylsulfur chlorid.. v

ourea bodies, contain sulfur and are insoluble in water, soluble insulfuric acid and in nitrobenzene givin colored solutions, sol.-

uble in the hydrosu fite vat, dyeing both cotchlor-methyl-sulfurchlorid, which coloring '40 matter possesses a composition correspondingto the formula consists when dry of'a brick-red powder, which yields anorange solution iii-concentrated sulfuric acid and a yellow solution inboiling nitrobenzene and which dyes cotton from the vat orange shades.

In testimony whereof I have hereunto set my hand in the presence of twosubscribing 3. As new articles of manufacture the col- Witnesses. oringmatters which can be obtained b 1' o MA HENRY ISLER- treating anamino-anthraquinone bod Witnesses: a trichlor-methyl-sulfur' c'hlorid,whic new J. ALEc. Limo),

coloring matters are dianthraquinonyl-thi- A. '0. TUTMANN:

